3-(((2-methoxyethoxy)methoxy)methyl)-6-(2-nitrophenyl)imidazo[2,1-b]thiazole | 1449583-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(((2-methoxyethoxy)methoxy)methyl)-6-(2-nitrophenyl)imidazo[2,1-b]thiazole
• CAS: 1449583-93-0
• 化学式: C₁₆H₁₇N₃O₅S
• 分子量: 363.394
• InChiKey: JOFWBQMLVGPYSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-(((2-methoxyethoxy)methoxy)methyl)-6-(2-nitrophenyl)imidazo[2,1-b]thiazole 在 吡啶 、 sodium hydrogen sulfide 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 39.0h， 生成 N-[2-[3-(2-methoxyethoxymethoxymethyl)imidazo[2,1-b][1,3]thiazol-6-yl]phenyl]quinoxaline-2-carboxamide
  参考文献：
  名称：

  Search for a novel SIRT1 activator: Structural modification of SRT1720 and biological evaluation

  摘要：

  Syntheses and biological evaluation of novel SRT1720 derivatives are described in search for new candidates of SIRT1 activator. Several parts of the SRT1720 structure, including piperazine moiety, quinoxaline ring on the amide group, and position of the amide function, were modified, and the assay results indicated that transfer of the ortho amide-substituent regarding to the imidazo[1,2-b]thiazole core onto the meta position resulted in improvement of SIRT1 activation ability. Modeling analyses of SRT1720 and the most potent derivative bound to model complex of SIRT1 with peptide substrate were also performed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.070
• 作为产物：
  描述：

  3-羟基甲基-6-(2-硝基苯基)咪唑并[2,1-b]噻唑 、 2-甲氧基乙氧基甲基氯 在 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以58%的产率得到3-(((2-methoxyethoxy)methoxy)methyl)-6-(2-nitrophenyl)imidazo[2,1-b]thiazole
  参考文献：
  名称：

  Search for a novel SIRT1 activator: Structural modification of SRT1720 and biological evaluation

  摘要：

  Syntheses and biological evaluation of novel SRT1720 derivatives are described in search for new candidates of SIRT1 activator. Several parts of the SRT1720 structure, including piperazine moiety, quinoxaline ring on the amide group, and position of the amide function, were modified, and the assay results indicated that transfer of the ortho amide-substituent regarding to the imidazo[1,2-b]thiazole core onto the meta position resulted in improvement of SIRT1 activation ability. Modeling analyses of SRT1720 and the most potent derivative bound to model complex of SIRT1 with peptide substrate were also performed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.070